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VP - Customer Success

for VP - Customer Success

About Milestone

Milestone Inc. is a leading Digital Experience Software and Services company focused on AI-first discovery, personalization, and conversion across all digital touchpoints. Our platform enables brands to be visible in search engines and AI answer engines through structured data, entity intelligence, and AI-driven orchestration.

We serve complex, multi-location enterprises across hospitality, banking/financial services, and MarTech-driven organizations, operating a hybrid SaaS + Services business model at scale.

VP - CS Role Overview

Milestone is seeking a strategic, revenue-oriented VP of Customer Experience & Success to own retention, expansion, partnerships, and customer outcomes across a global customer base.

This is a revenue-adjacent executive role, accountable for GRR, NRR, churn reduction, expansion ARR, payback period, and customer lifetime value—not just customer satisfaction.

The VP - CS will design and operate a modern, AI-powered Customer Success engine, spanning onboarding through expansion, while leading distributed teams across the US, India, Canada, and Mexico.

Problems We Are Looking to Solve

The VP - CS will be entrusted with solving systemic, enterprise-level challenges including:

  • Lifecycle execution challenges across onboarding, adoption, renewal, and expansion
  • Limited predictability in churn risk, renewals, and expansion forecasting
  • Scalability and repeatability in CS playbooks
  • Fragmentation across SaaS + Services delivery models
  • Underutilization of AI and automation in CS workflows
  • Weak executive-level customer relationships in complex verticals

Key Responsibilities

1. Strategic Customer Success & Revenue Ownership

  • Own and improve GRR, NRR, churn, expansion ARR, CLV, and cohort health
  • Operate and forecast a multi-million-dollar global book of business
  • Design and run end-to-end scalable and repeatable lifecycle playbooks:
    • Onboarding → Adoption → Value Realization → Renewal → Expansion
  • Establish a rigorous operating cadence:
    • QBRs, executive reviews, health scoring, churn risk models, expansion pipelines
  • Directly align CS outcomes with Company OKRs and board-level metrics
  • Own the creation of systematic, built-in expansion engines so that customers adopting the platform have defined, automatic ARR growth year over year.

2. Global Leadership & Operating Rigor

  • Lead and scale 60+ global team members across CS, PS, Support, and CS Ops
  • Implement clear playbooks, SLAs, escalation models, and governance
  • Drive cross-functional alignment with Sales, Product, Marketing, Engineering, and Delivery
  • Lead change management for:
    • New processes
    • Pricing & packaging shifts
    • AI-enabled workflows and tooling

3. MarTech, Hospitality & Banking Domain Leadership

  • Bring deep expertise in MarTech ecosystems:
    • CDPs, CRMs, personalization, attribution, ABM, campaign orchestration
  • Demonstrate direct experience serving hospitality and banking / financial services clients
  • Translate platform capabilities into vertical-specific business outcomes
  • Act as an executive partner to CMOs, CDOs, Heads of Digital & Loyalty

4. AI, Automation & CS Technology Leadership

  • Deploy AI-driven Customer Success capabilities, including:
    • Predictive health scoring
    • Churn and risk signals
    • Automated play triggers & next-best-action systems
    • Renewal and expansion forecasting
  • Drive automation across the CS stack:
    • CRM, ticketing, in-app guidance, chatbots, knowledge bases
  • Improve:
    • Time-to-value
    • CS productivity
    • Margin and scalability

5. Hybrid SaaS + Services Model Excellence

  • Operate across:
    • Recurring SaaS (land-and-expand, usage-driven models)
    • Services (projects, retainers, SOWs, campaigns)
  • Define clear value, scope, and success metrics for blended offerings
  • Partner with CS Ops / Rev Ops to standardize:
    • Handoffs
    • Capacity planning
    • Margin and profitability tracking
  • Replace hero-driven delivery with repeatable, scalable execution models

6. Executive, Entrepreneurial & Culture Leadership

  • Bring an entrepreneurial mindset suited for ambiguity and scale
  • Build a strong CS leadership bench in the Bay Area while leveraging global teams
  • Demonstrate executive presence through:
    • Board-level storytelling
    • Strategic customer engagement
    • Partner and ecosystem leadership
  • Serve as a culture carrier, reinforcing:
    • Ownership over activity
    • Accountability over intent
    • Customer obsession over internal comfort

7. Product Mindset & MarTech Leadership Expectations

  • Bring a strong product mindset beyond support and service delivery
  • Partner with Product, Engineering, and Go-to-Market teams to influence roadmap priorities
  • Understand modern MarTech ecosystems including CDPs, CRM, personalization, attribution, SEO/discovery, analytics, and AI-driven engagement
  • Translate customer pain points into platform enhancements and automation opportunities
  • Use data-driven insights from adoption, retention, and usage to improve lifecycle performance
  • Experience in fast-paced SaaS environments where CS drives adoption and monetization
  • Understand enterprise digital transformation across hospitality, banking, and MarTech sectors

Ideal Candidate Profile

  • Thinks in outcomes, revenue, and systems
  • Operates comfortably with C-suite buyers
  • Understands SaaS economics and services margin
  • Builds scalable operating models while executing effectively
  • Credible with boards, customers, and frontline teams
  • Strong learning mindset

Required Experience & Qualifications

  • 15-20+ years in SaaS, MarTech platforms, agencies, or B2B environments
  • VP or Sr Director experience in retention and expansion
  • High-growth/startup experience required
  • Strong command of CS economics (GRR, NRR, churn, expansion, CLV)
  • Experience in hospitality and/or banking verticals
  • Global leadership across multi-time-zone teams
  • Bay Area presence preferred

Key Focus Areas (2026 Lens)

  • Revenue retention and expansion predictability
  • Lifecycle playbook standardization
  • AI-powered CS workflows
  • Executive customer partnerships
  • Margin improvement across SaaS + Services
  • Partnership and agency program growth

KPI & Metrics Ownership

  • Gross Revenue Retention (GRR)
  • Net Revenue Retention (NRR)
  • Churn Rate (Logo & Revenue)
  • Expansion ARR
  • Customer Lifetime Value (CLV)
  • Time-to-Value
  • Renewal Forecast Accuracy
  • CS Productivity & Margin
  • Customer Sentiment (NPS / CSAT)
  • AI Automation Adoption & Efficiency Gains

What Success Looks Like (First 12-18 Months)

  • Measurable improvement in GRR, NRR, and churn reduction
  • Globally adopted lifecycle playbooks
  • Predictable renewal and expansion forecasting
  • AI-driven CS workflows delivering efficiency gains
  • Strong executive relationships across top accounts
  • A scalable, high-performing global CS leadership team

Why Milestone

  • Founder-led, award-winning, AI-first platform
  • Deep focus on GEO, AI visibility, and customer outcomes
  • Opportunity to shape Customer Success as a true growth engine
  • Certified Great Place to Work